Tetrahydrofuran → N~1~-Methylcyclohexane-1,4-diamine

Amine 1 (15.0 g, 0.7 mol) was added slowly over 45 min to a 1N solution of lithium aluminium hydride in THF (450 mL, 0.36 mol) under nitrogen. The mixture was stirred for 30 min at room temperature, then heated at reflux for 5-6 hours under nitrogen. Water (13.2 mL) was added to the mixture followed by 15% aqueous sodium hydroxide (13.2 mL), and water (39.7 mL). The mixture was then stirred for 15-30 min. The solid was filtered off and washed with t-butylmethyl ether (200 mL), dichloromethane (200 mL), and t-butylmethyl ether (200 mL). The organic extracts were collected, dried (MgSO4), and filtered. The drying agent was then washed with dichloromethane and the organic extracts combined and concentrated in vacuo to give the title compound 2 (7.52 g, 84%) as a pale yellow solid: δH (360 MHz: CDCl3) 1.04-1.20 (q, 4H), 1.51 (br s, 3H), 1.80-1.96 (m, 4H), 2.25-2.35 (m, 1H), 2.41 (s, 3H), 2.61-2.72 (m, 1H).

1. temperatureheated
2. temperatureat reflux for 5-6 hours under nitrogen
3. stirringThe mixture was then stirred for 15-30 min
4. filtrationThe solid was filtered off
5. washwashed with t-butylmethyl ether (200 mL), dichloromethane (200 mL), and t-butylmethyl ether (200 mL)
6. customThe organic extracts were collected
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. washThe drying agent was then washed with dichloromethane
10. concentrationconcentrated in vacuo

ORD record

ord-f4e8e77cf0254a5ca17eb46b9c8e13b4

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613798B1